O^2',O⁷-Bis(triethylsilyl)taxol | 135365-62-7

• 英文名称: O^2',O⁷-Bis(triethylsilyl)taxol
• 英文别名: 2',7'-bis(diethylsilyl)taxol；[(1S,2S,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-3-phenyl-2-triethylsilyloxypropanoyl]oxy-1-hydroxy-10,14,17,17-tetramethyl-11-oxo-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 135365-62-7；149197-24-0
• 化学式: C₅₉H₇₉NO₁₄Si₂
• 分子量: 1082.45
• InChiKey: WPGSFSCXNLAODB-DYTQNEOJSA-N

物化性质

• 沸点：
  967.2±65.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、乙醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  9.79
• 重原子数：
  76
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  199
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  O^2',O⁷-Bis(triethylsilyl)taxol 在 吡啶 、 氟化氢吡啶 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 96.0h， 生成 (1α)-15(16)-anhydro-11(15->1)abeotaxol
  参考文献：
  名称：

  Modified taxols. 5. Reaction of taxol with electrophilic reagents and preparation of a rearranged taxol derivative with tubulin assembly activity

  摘要：

  Reaction of the antineoplastic natural product taxol (1) with Meerwein's reagent leads to a product 4 with an opened oxetane ring. Reaction of taxol with acetyl chloride yields a product 16 in which the oxetane ring is opened and the A ring is contracted; a taxol derivative with a contracted A ring alone (22) can be prepared from taxol on treatment with mesyl chloride. The ring-contracted taxol derivative 22 shows comparable activity to taxol in a tubulin disassembly assay, but does not show significant cytotoxicity against KB cells in a cell culture assay; the derivatives 4 and 16 are inactive in both assays.

  DOI：

  10.1021/jo00017a024
• 作为产物：
  描述：

  三乙基氯硅烷 、 paclitaxel 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以96%的产率得到O^2',O⁷-Bis(triethylsilyl)taxol
  参考文献：
  名称：

  Modified taxols. 5. Reaction of taxol with electrophilic reagents and preparation of a rearranged taxol derivative with tubulin assembly activity

  摘要：

  Reaction of the antineoplastic natural product taxol (1) with Meerwein's reagent leads to a product 4 with an opened oxetane ring. Reaction of taxol with acetyl chloride yields a product 16 in which the oxetane ring is opened and the A ring is contracted; a taxol derivative with a contracted A ring alone (22) can be prepared from taxol on treatment with mesyl chloride. The ring-contracted taxol derivative 22 shows comparable activity to taxol in a tubulin disassembly assay, but does not show significant cytotoxicity against KB cells in a cell culture assay; the derivatives 4 and 16 are inactive in both assays.

  DOI：

  10.1021/jo00017a024